Jennings holds the title of having the longest run of consecutive games won, while Rutter's $3.2 million purse makes him the largest money winner. Both offered insights into some of their winning strategies going into the three-day, two-game Jeopardy challenge with Big Blue's (IBM) Watson.

But those figures don't deter Watson's human challengers. "He's faster on the buzzer and more consistent, so I'll have to bet more aggressively," says Jennings -- who jokes that he has to win this one for the underdog in this contest, the human race. He plans to wager more of his winnings on any Jeopardy Daily Doubles that come up in the game.

Rutter says he's looking forward to certain game categories where he thinks Watson might be slow to answer, such as questions where the cues are very short or more abstract.

"The 'Before and After' category is an example of one I'd do," says Rutter. "There's a lot of word play." He notes humans have the advantage in the word-play categories, compared to fact-based questions.

Beating Watson to the Punch

Jennings and Rutter also are prepared for Watson to aggressively search for Daily Doubles that, if answered correctly, can beef up a contestant's winnings in a matter of seconds.

During the practice rounds, Watson reportedly played in a very traditional fashion of picking a category and working its way from the top of the board to the bottom. But in real play, according to Jennings and Rutter, Watson suddenly became hyper-vigilant in searching for Daily Doubles, which are often found in the last three rows of the board.

As a result, Rutter says, he plans to jump in earlier and try to claim as many Daily Doubles as he can before Watson finds them.

And while they don't get any extra points for being human, Jennings joked that Jeopardy host Alex Trebek said the two human challengers may have to compensate for Watson's deadpan ways.

"He said we need to be funnier than usual," says Jennings, "because Watson won't be carrying the show."